| Date & Time | Game | Venue |
|---|---|---|
| January 02, 2021 | (0) Weymouth Wildcats at (7) Wellesley Raiders | Wellesley Sports Center |
| January 06, 2021 | (5) Needham Rockets at (2) Weymouth Wildcats | Connell Memorial Rink |
| Jan. 9 Postponed | Weymouth Wildcats at Needham Rockets | Babson Skating Center |
| Jan. 13 Postponed | Weymouth Wildcats at Braintree Wamps | Zapustas Arena |
| Jan. 20 Postponed | Walpole Timberwolves at Weymouth Wildcats | Connell Memorial Rink |
| Jan. 23 Postponed | Weymouth Wildcats at Walpole Timberwolves | Rodman Arena |
| January 27, 2021 | (5) Weymouth Wildcats at (2) Milton Wildcats | Ulin Memorial Rink |
| January 30, 2021 | (3) Milton Wildcats at (2) Weymouth Wildcats | Connell Memorial Rink |
| Feb. 3 Postponed | Weymouth Wildcats at Newton North/South Tigers | Fessenden School Rink |
| February 06, 2021 | (1) Newton North/South Tigers at (6) Weymouth Wildcats | Connell Memorial Rink |
| February 15, 2021 | (1) Archbishop Williams Bishops at (2) Weymouth Wildcats | Connell Memorial Rink |
| February 17, 2021 | (3) Whitman-Hanson/Silver Lake Panthers at (5) Weymouth Wildcats | Connell Memorial Rink |
